US5589326A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Osmium-containing redox mediator
Assignee: Roche Diabetes Care Inc
•
Filing: 1993-12-30
•
Granted: 1996-12-31
•
Expires: 2013-12-30
Abstract
Abstract A new group of Os(II) and Os(III) compounds useful as redox mediators in electrochemical biosensors. These compounds have 1) low oxidation potential, 2) fast reaction kinetics between the electroactive center of an enzyme and the compound, 3) slow oxidation of osmium by oxygen, and 4) excellent solubility in aqueous medium. These mediators are particularly useful as a component of a reagent used in an electrochemical biosensor, wherein the biosensor is useful for measuring analytes from a biological fluid, such as blood.
Inventors
- 👤 Zhi D. Deng
- 👤 Gerald F. Sigler
- 👤 Nigel A. Surridge
- 👤 Christopher D. Wilsey
- 👤 Robert J. McEnroe
- 👤 Walter W. Jernigan
- 👤 Rebecca W. Muddiman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:56
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/0006; C07F15/002; C07F15/0026; C12; C12Q; C12Q1/00; C12Q1/001; C12Q1/004; Y; Y10; Y10S; Y10S435/00; Y10S435/817
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
138 words
A compound having the formula: ##STR5## wherein R and R' are the same or different and are 2,2'-bipyridyl, 4,4'-disubstituted-2,2'-bipyridyl, 5,5'-disubstituted-2,2'-bipyridyl, 1,10-phenanthrolinyl, 4,7-disubstituted-1,10-phenanthrolinyl, or 5,6-disubstituted-1,10-phenanthrolinyl, wherein the disubstitution is a methyl, ethyl, or phenyl group, R and R' are coordinated to Os at their nitrogen atoms, R" is hydrogen, methyl or ethyl, Z is chloro or bromo, m is +1 or +2, X is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate, nitrate, sulfate, carbonate, or sulfite, Y is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate or nitrate, and n is 1 or zero, but when X is sulfate, carbonate, or sulfite, n is zero, and when m is 1, n is zero and X is not sulfate, carbonate or sulfite, wherein the aqueous solubility of the compound is greater than about 1 millimolar.
Claim 2
Dependent Claim
138 words
A compound having the formula: ##STR5## wherein R and R' are the same or different and are 2,2'-bipyridyl, 4,4'-disubstituted-2,2'-bipyridyl, 5,5'-disubstituted-2,2'-bipyridyl, 1,10-phenanthrolinyl, 4,7-disubstituted-1,10-phenanthrolinyl, or 5,6-disubstituted-1,10-phenanthrolinyl, wherein the disubstitution is a methyl, ethyl, or phenyl group, R and R' are coordinated to Os at their nitrogen atoms, R" is hydrogen, methyl or ethyl, Z is chloro or bromo, m is +1 or +2, X is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate, nitrate, sulfate, carbonate, or sulfite, Y is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate or nitrate, and n is 1 or zero, but when X is sulfate, carbonate, or sulfite, n is zero, and when m is 1, n is zero and X is not sulfate, carbonate or sulfite, wherein the aqueous solubility of the compound is greater than about 1 millimolar.
Claim 3
Dependent Claim
32 words
The compound of claim 1, wherein R and R' are the same or different and are 2,2'-bipyridyl, 4,4'-disubstituted-2,2'-bipyridyl, or 5,5'-disubstituted 2,2'-bipyridyl, wherein the disubstitution may be a methyl, ethyl, or phenyl group.
Claim 4
Dependent Claim
11 words
The compound of claim 2, wherein R" is hydrogen or methyl.
Claim 5
Dependent Claim
9 words
The compound of claim 3, wherein Z is chloro.
Claim 6
Dependent Claim
42 words
The compound of claim 4, wherein X is an anion and is chloride, bromide, or tetrafluoroborate, Y is an anion and is chloride, bromide, or tetrafluoroborate, and when m is 2, n is 1 and when m is 1, n is zero.
Claim 7
Dependent Claim
11 words
The compound of claim 1, wherein R and R' are 2,2'-bipyridyl.
Claim 8
Dependent Claim
11 words
The compound of claim 6, wherein R" is hydrogen or methyl.
Claim 9
Dependent Claim
9 words
The compound of claim 7, wherein Z is chloro.
Claim 10
Dependent Claim
42 words
The compound of claim 8, wherein X is an anion and is chloride, bromide, or tetrafluoroborate, Y is an anion and is chloride, bromide, or tetrafluoroborate, and when m is 2, n is 1 and when m is 1, n is zero.
Claim 11
Dependent Claim
43 words
The compound of claim 9, wherein R" is hydrogen, X is an anion and is chloride or tetrafluoroborate, Y is an anion and is chloride or tetrafluoroborate, and when m is 2, n is 1 and when m is 1, n is zero.
Claim 12
Dependent Claim
129 words
A compound having the formula: ##STR6## wherein R and R' are the same or different and are 2,2'-bipyridyl, 4,4'-dimethyl-2,2'-bipyridyl, 4,4'-diphenyl-2,2'-bipyridyl, 1,10-phenanthrolinyl, 4,7-dimethyl-1,10-phenanthrolinyl, 4,7-diphenyl-1,10-phenanthrolinyl, or 5,6-dimethyl-1,10-phenanthrolinyl, R and R' are coordinated to Os at their nitrogen atoms, R" is hydrogen, methyl or ethyl, Z is chloro or bromo, m is +1 or +2, X is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate, nitrate, sulfate, carbonate, or sulfite, Y is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate or nitrate, and n is 1 or zero, but when X is sulfate, carbonate, or sulfite, n is zero, and when m is 1, n is zero and X is not sulfate, carbonate or sulfite, wherein the aqueous solubility of the compound is greater than about 1 millimolar.
Claim 13
Dependent Claim
129 words
A compound having the formula: ##STR6## wherein R and R' are the same or different and are 2,2'-bipyridyl, 4,4'-dimethyl-2,2'-bipyridyl, 4,4'-diphenyl-2,2'-bipyridyl, 1,10-phenanthrolinyl, 4,7-dimethyl-1,10-phenanthrolinyl, 4,7-diphenyl-1,10-phenanthrolinyl, or 5,6-dimethyl-1,10-phenanthrolinyl, R and R' are coordinated to Os at their nitrogen atoms, R" is hydrogen, methyl or ethyl, Z is chloro or bromo, m is +1 or +2, X is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate, nitrate, sulfate, carbonate, or sulfite, Y is an anion and is chloride, bromide, iodide, fluoride, tetrafluoroborate, perchlorate or nitrate, and n is 1 or zero, but when X is sulfate, carbonate, or sulfite, n is zero, and when m is 1, n is zero and X is not sulfate, carbonate or sulfite, wherein the aqueous solubility of the compound is greater than about 1 millimolar.
References Cited (Backward Citations)
US4381978A
Cited
US4293310A
Cited
US4545382A
Cited
US4526661A
Cited
EP0096288B1
Cited
US4711245A
Cited
EP0127958B1
Cited
US4954414A
Cited
US5288636A
Cited
WO1992014836A1
Cited
WO1992014741A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-12-31 | 2000-07-01 | 2000-12-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-12-31 | 2004-07-01 | 2004-12-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-12-31 | 2008-07-01 | 2008-12-31 | $7700.00 | Window Closed / Lapsed |